diff --git a/cmd/entire/cli/resume.go b/cmd/entire/cli/resume.go
index 7d597f6b1..686cc6de6 100644
--- a/cmd/entire/cli/resume.go
+++ b/cmd/entire/cli/resume.go
@@ -7,6 +7,7 @@ import (
 	"log/slog"
 	"os"
 	"path/filepath"
+	"sort"
 
 	"github.com/entireio/cli/cmd/entire/cli/agent"
 	"github.com/entireio/cli/cmd/entire/cli/checkpoint"
@@ -420,6 +421,12 @@ func resumeSession(sessionID string, checkpointID id.CheckpointID, force bool) e
 			return resumeSingleSession(ctx, ag, sessionID, checkpointID, repoRoot, force)
 		}
 
+		// Sort sessions by CreatedAt so the most recent is last (for display).
+		// This fixes ordering when subdirectory index doesn't reflect activity order.
+		sort.Slice(sessions, func(i, j int) bool {
+			return sessions[i].CreatedAt.Before(sessions[j].CreatedAt)
+		})
+
 		logging.Debug(ctx, "resume session completed",
 			slog.String("checkpoint_id", checkpointID.String()),
 			slog.Int("session_count", len(sessions)),
diff --git a/cmd/entire/cli/strategy/manual_commit_rewind.go b/cmd/entire/cli/strategy/manual_commit_rewind.go
index 54ec9a596..ef739dd48 100644
--- a/cmd/entire/cli/strategy/manual_commit_rewind.go
+++ b/cmd/entire/cli/strategy/manual_commit_rewind.go
@@ -699,6 +699,7 @@ func (s *ManualCommitStrategy) RestoreLogsOnly(point RewindPoint, force bool) ([
 			SessionID: sessionID,
 			Agent:     sessionAgent.Type(),
 			Prompt:    promptPreview,
+			CreatedAt: content.Metadata.CreatedAt,
 		})
 	}
 
diff --git a/cmd/entire/cli/strategy/strategy.go b/cmd/entire/cli/strategy/strategy.go
index 4ce450093..48e83f9ee 100644
--- a/cmd/entire/cli/strategy/strategy.go
+++ b/cmd/entire/cli/strategy/strategy.go
@@ -473,6 +473,7 @@ type RestoredSession struct {
 	SessionID string
 	Agent     agent.AgentType
 	Prompt    string
+	CreatedAt time.Time // From session metadata; used by resume to determine most recent
 }
 
 // LogsOnlyRestorer is an optional interface for strategies that support